My issue with Suit Supply is their drop. They have a 6" drop. I'm a 42R and a 32-24" in the waist... Without the option to pick waist size, I'm left with a 36" waist which is up to 4" too big. Naturally trousers bigger in the waste will be wider legs as well (though if I alter the pants, I might have enough fabric to make a cape haha)... I ordered a Napoli and after finding this out, cancelled and got a refund. Too bad their suits aren't as good as their customer...

http://www.mensitaly.com/Pimp-Suits/Pimp-Suits.html
If you can't find a similar one to the above, I'm sure there's a comparable suit in quality and with more flare. Might I suggest you order it a couple sizes too big as well.

Johnston & Murphy has a few pairs of dress shoes with rubber soles, meant for winter months. I will say, however, that there is no real offense to salt. Make sure you wipe clean your shoes everyday after walking through any salted areas.
http://www.johnstonmurphy.com/product.aspx?c=1215&sc=1215&sid=Shoes&pid=91267
There's also a Lefler Cap Toe and a Lefler Chukka in leather. Good luck

Anyone know the proper way so I don't ruin my new shoes? Best advice would be just to wear them around the house to break them in. This will allow them to form to your foot, better than any bending might do. Good luck.

Try J. Crew; they have a suit line that is more work/ play than strictly work... with different fabrics and unique prints that can be business enough to wear in the office and casual enough to take to the streets. It sounds like you have enough dress shirts, though might I recommend some button downs. These can be worn unbuttoned or with tie, if need be. Look into a few cardigans and v-neck sweaters that can be worn to work for the winter days (i.e. over a button down,...